#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:33:58 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178625 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/36/4073614.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4073614
loop_
_publ_author_name
'Fischer, Paul J.'
'Herm, Zoey R.'
'Kucera, Benjamin E.'
_publ_section_title
;
 [(2-(Trimethylammonium)ethyl)cyclopentadienyl]tricarbonylmetalates: 
 Group VI Metal Zwitterions
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              4680
_journal_paper_doi               10.1021/om700497z
_journal_volume                  26
_journal_year                    2007
_chemical_formula_moiety         'C13 H17 Cr I N O3, I'
_chemical_formula_sum            'C13 H17 Cr I2 N O3'
_chemical_formula_weight         541.08
_chemical_name_common            06189
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.3940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0640(9)
_cell_length_b                   9.9270(7)
_cell_length_c                   13.9859(10)
_cell_measurement_reflns_used    3141
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.52
_cell_volume                     1813.2(2)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12610
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    4.041
_exptl_absorpt_correction_T_max  0.8884
_exptl_absorpt_correction_T_min  0.3769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.416
_refine_diff_density_min         -1.082
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0341P)²+5.3938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                3228
_reflns_number_total             3712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om700497z.cif
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4073614
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I -0.05044(2) 0.61292(3) 0.22532(2) 0.03423(10) Uani 1 1 d .
I2 I 0.55761(2) 0.22192(3) 0.64499(2) 0.02740(9) Uani 1 1 d .
Cr1 Cr 0.13826(5) 0.67711(7) 0.14942(5) 0.02233(16) Uani 1 1 d .
O1 O -0.0127(4) 0.8181(5) 0.0151(3) 0.0629(13) Uani 1 1 d .
O2 O 0.2466(4) 0.9403(4) 0.1225(4) 0.0653(13) Uani 1 1 d .
O3 O 0.1518(3) 0.7742(4) 0.3545(2) 0.0417(9) Uani 1 1 d .
N1 N 0.3621(3) 0.2856(4) 0.3882(3) 0.0248(8) Uani 1 1 d .
C1 C 0.0426(4) 0.7637(5) 0.0669(4) 0.0397(12) Uani 1 1 d .
C2 C 0.2039(4) 0.8406(5) 0.1329(4) 0.0409(12) Uani 1 1 d .
C3 C 0.1451(4) 0.7389(5) 0.2777(3) 0.0287(10) Uani 1 1 d .
C4 C 0.2257(3) 0.4975(4) 0.1954(3) 0.0224(9) Uani 1 1 d .
C5 C 0.1453(3) 0.4537(4) 0.1328(3) 0.0253(9) Uani 1 1 d .
H5 H 0.0898 0.3888 0.1493 0.030 Uiso 1 1 calc R
C6 C 0.1571(4) 0.5161(5) 0.0435(3) 0.0309(10) Uani 1 1 d .
H6 H 0.1124 0.5012 -0.0146 0.037 Uiso 1 1 calc R
C7 C 0.2451(4) 0.5961(5) 0.0479(3) 0.0299(10) Uani 1 1 d .
H7 H 0.2756 0.6459 -0.0067 0.036 Uiso 1 1 calc R
C8 C 0.2877(4) 0.5853(5) 0.1420(3) 0.0293(10) Uani 1 1 d .
H8 H 0.3535 0.6268 0.1650 0.035 Uiso 1 1 calc R
C9 C 0.2467(4) 0.4516(4) 0.2968(3) 0.0269(9) Uani 1 1 d .
H9A H 0.1814 0.4381 0.3298 0.032 Uiso 1 1 calc R
H9B H 0.2869 0.5210 0.3320 0.032 Uiso 1 1 calc R
C10 C 0.3063(3) 0.3204(4) 0.2949(3) 0.0222(9) Uani 1 1 d .
H10A H 0.3570 0.3256 0.2436 0.027 Uiso 1 1 calc R
H10B H 0.2583 0.2463 0.2784 0.027 Uiso 1 1 calc R
C11 C 0.2920(4) 0.2931(5) 0.4707(3) 0.0399(12) Uani 1 1 d .
H11A H 0.3268 0.2572 0.5281 0.060 Uiso 1 1 calc R
H11B H 0.2303 0.2399 0.4565 0.060 Uiso 1 1 calc R
H11C H 0.2728 0.3872 0.4818 0.060 Uiso 1 1 calc R
C12 C 0.4004(4) 0.1436(5) 0.3807(4) 0.0348(11) Uani 1 1 d .
H12A H 0.4412 0.1210 0.4382 0.052 Uiso 1 1 calc R
H12B H 0.4430 0.1351 0.3243 0.052 Uiso 1 1 calc R
H12C H 0.3421 0.0819 0.3748 0.052 Uiso 1 1 calc R
C13 C 0.4512(4) 0.3786(5) 0.4037(3) 0.0326(11) Uani 1 1 d .
H13A H 0.4877 0.3546 0.4633 0.049 Uiso 1 1 calc R
H13B H 0.4265 0.4716 0.4078 0.049 Uiso 1 1 calc R
H13C H 0.4977 0.3706 0.3501 0.049 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 Cr1 C1 80.0(3)
C2 Cr1 C3 79.8(2)
C1 Cr1 C3 116.5(2)
C2 Cr1 C8 86.7(2)
C1 Cr1 C8 138.5(2)
C3 Cr1 C8 99.24(19)
C2 Cr1 C7 86.3(2)
C1 Cr1 C7 101.3(2)
C3 Cr1 C7 136.32(19)
C8 Cr1 C7 38.31(17)
C2 Cr1 C6 119.6(2)
C1 Cr1 C6 90.2(2)
C3 Cr1 C6 150.44(19)
C8 Cr1 C6 62.88(18)
C7 Cr1 C6 37.32(18)
C2 Cr1 C4 120.4(2)
C1 Cr1 C4 151.3(2)
C3 Cr1 C4 88.50(18)
C8 Cr1 C4 37.82(16)
C7 Cr1 C4 63.54(16)
C6 Cr1 C4 62.78(16)
C2 Cr1 C5 146.8(2)
C1 Cr1 C5 114.6(2)
C3 Cr1 C5 114.79(18)
C8 Cr1 C5 62.37(17)
C7 Cr1 C5 62.29(17)
C6 Cr1 C5 36.99(16)
C4 Cr1 C5 37.33(16)
C2 Cr1 I1 131.71(17)
C1 Cr1 I1 75.98(17)
C3 Cr1 I1 74.62(15)
C8 Cr1 I1 137.09(13)
C7 Cr1 I1 139.03(14)
C6 Cr1 I1 101.85(13)
C4 Cr1 I1 99.28(11)
C5 Cr1 I1 81.43(12)
C11 N1 C13 110.3(4)
C11 N1 C12 108.2(4)
C13 N1 C12 109.3(4)
C11 N1 C10 111.2(4)
C13 N1 C10 109.8(3)
C12 N1 C10 107.9(3)
O1 C1 Cr1 177.6(5)
O2 C2 Cr1 178.4(5)
O3 C3 Cr1 178.0(4)
C8 C4 C5 106.7(4)
C8 C4 C9 126.1(4)
C5 C4 C9 127.0(4)
C8 C4 Cr1 69.3(3)
C5 C4 Cr1 72.4(2)
C9 C4 Cr1 126.9(3)
C6 C5 C4 108.5(4)
C6 C5 Cr1 70.2(3)
C4 C5 Cr1 70.3(2)
C6 C5 H5 125.8
C4 C5 H5 125.8
Cr1 C5 H5 125.8
C7 C6 C5 108.7(4)
C7 C6 Cr1 70.3(3)
C5 C6 Cr1 72.9(2)
C7 C6 H6 125.6
C5 C6 H6 125.6
Cr1 C6 H6 125.6
C6 C7 C8 107.5(4)
C6 C7 Cr1 72.4(3)
C8 C7 Cr1 70.4(3)
C6 C7 H7 126.2
C8 C7 H7 126.2
Cr1 C7 H7 126.2
C4 C8 C7 108.6(4)
C4 C8 Cr1 72.8(3)
C7 C8 Cr1 71.3(3)
C4 C8 H8 125.6
C7 C8 H8 125.6
Cr1 C8 H8 125.6
C4 C9 C10 109.0(3)
C4 C9 H9A 109.9
C10 C9 H9A 109.9
C4 C9 H9B 109.9
C10 C9 H9B 109.9
H9A C9 H9B 108.3
C9 C10 N1 114.6(3)
C9 C10 H10A 108.6
N1 C10 H10A 108.6
C9 C10 H10B 108.6
N1 C10 H10B 108.6
H10A C10 H10B 107.6
N1 C11 H11A 109.5
N1 C11 H11B 109.5
H11A C11 H11B 109.5
N1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N1 C12 H12A 109.5
N1 C12 H12B 109.5
H12A C12 H12B 109.5
N1 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N1 C13 H13A 109.5
N1 C13 H13B 109.5
H13A C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 Cr1 2.7817(8)
Cr1 C2 1.853(6)
Cr1 C1 1.887(5)
Cr1 C3 1.896(5)
Cr1 C8 2.159(5)
Cr1 C7 2.170(5)
Cr1 C6 2.197(4)
Cr1 C4 2.205(4)
Cr1 C5 2.232(4)
O1 C1 1.146(6)
O2 C2 1.147(7)
O3 C3 1.131(6)
N1 C11 1.492(6)
N1 C13 1.497(6)
N1 C12 1.501(6)
N1 C10 1.519(5)
C4 C8 1.415(6)
C4 C5 1.420(6)
C4 C9 1.508(6)
C5 C6 1.405(6)
C5 H5 1.0000
C6 C7 1.398(7)
C6 H6 1.0000
C7 C8 1.421(6)
C7 H7 1.0000
C8 H8 1.0000
C9 C10 1.518(6)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 Cr1 C1 O1 39(13)
C3 Cr1 C1 O1 112(13)
C8 Cr1 C1 O1 -34(13)
C7 Cr1 C1 O1 -45(13)
C6 Cr1 C1 O1 -81(13)
C4 Cr1 C1 O1 -99(13)
C5 Cr1 C1 O1 -109(13)
I1 Cr1 C1 O1 177(100)
C1 Cr1 C2 O2 -136(19)
C3 Cr1 C2 O2 104(19)
C8 Cr1 C2 O2 4(19)
C7 Cr1 C2 O2 -34(19)
C6 Cr1 C2 O2 -52(19)
C4 Cr1 C2 O2 22(19)
C5 Cr1 C2 O2 -16(20)
I1 Cr1 C2 O2 163(19)
C2 Cr1 C3 O3 -88(13)
C1 Cr1 C3 O3 -161(13)
C8 Cr1 C3 O3 -3(13)
C7 Cr1 C3 O3 -14(13)
C6 Cr1 C3 O3 47(13)
C4 Cr1 C3 O3 34(13)
C5 Cr1 C3 O3 61(13)
I1 Cr1 C3 O3 134(13)
C2 Cr1 C4 C8 -30.0(3)
C1 Cr1 C4 C8 100.9(5)
C3 Cr1 C4 C8 -107.2(3)
C7 Cr1 C4 C8 38.0(3)
C6 Cr1 C4 C8 80.0(3)
C5 Cr1 C4 C8 116.2(4)
I1 Cr1 C4 C8 178.6(2)
C2 Cr1 C4 C5 -146.2(3)
C1 Cr1 C4 C5 -15.3(5)
C3 Cr1 C4 C5 136.6(3)
C8 Cr1 C4 C5 -116.2(4)
C7 Cr1 C4 C5 -78.2(3)
C6 Cr1 C4 C5 -36.2(3)
I1 Cr1 C4 C5 62.4(2)
C2 Cr1 C4 C9 90.3(4)
C1 Cr1 C4 C9 -138.8(5)
C3 Cr1 C4 C9 13.1(4)
C8 Cr1 C4 C9 120.3(5)
C7 Cr1 C4 C9 158.3(4)
C6 Cr1 C4 C9 -159.7(4)
C5 Cr1 C4 C9 -123.5(5)
I1 Cr1 C4 C9 -61.1(4)
C8 C4 C5 C6 -1.2(5)
C9 C4 C5 C6 -176.7(4)
Cr1 C4 C5 C6 60.0(3)
C8 C4 C5 Cr1 -61.2(3)
C9 C4 C5 Cr1 123.3(4)
C2 Cr1 C5 C6 -57.9(5)
C1 Cr1 C5 C6 52.8(3)
C3 Cr1 C5 C6 -168.4(3)
C8 Cr1 C5 C6 -80.8(3)
C7 Cr1 C5 C6 -37.3(3)
C4 Cr1 C5 C6 -119.2(4)
I1 Cr1 C5 C6 123.0(3)
C2 Cr1 C5 C4 61.3(5)
C1 Cr1 C5 C4 172.0(3)
C3 Cr1 C5 C4 -49.2(3)
C8 Cr1 C5 C4 38.4(2)
C7 Cr1 C5 C4 81.9(3)
C6 Cr1 C5 C4 119.2(4)
I1 Cr1 C5 C4 -117.8(2)
C4 C5 C6 C7 1.4(5)
Cr1 C5 C6 C7 61.5(3)
C4 C5 C6 Cr1 -60.1(3)
C2 Cr1 C6 C7 30.0(4)
C1 Cr1 C6 C7 108.6(3)
C3 Cr1 C6 C7 -96.0(4)
C8 Cr1 C6 C7 -38.5(3)
C4 Cr1 C6 C7 -81.3(3)
C5 Cr1 C6 C7 -117.8(4)
I1 Cr1 C6 C7 -175.7(2)
C2 Cr1 C6 C5 147.8(3)
C1 Cr1 C6 C5 -133.6(3)
C3 Cr1 C6 C5 21.8(5)
C8 Cr1 C6 C5 79.3(3)
C7 Cr1 C6 C5 117.8(4)
C4 Cr1 C6 C5 36.5(3)
I1 Cr1 C6 C5 -57.9(3)
C5 C6 C7 C8 -1.1(5)
Cr1 C6 C7 C8 62.1(3)
C5 C6 C7 Cr1 -63.1(3)
C2 Cr1 C7 C6 -154.2(3)
C1 Cr1 C7 C6 -75.1(3)
C3 Cr1 C7 C6 134.7(3)
C8 Cr1 C7 C6 116.6(4)
C4 Cr1 C7 C6 79.1(3)
C5 Cr1 C7 C6 36.9(3)
I1 Cr1 C7 C6 6.4(4)
C2 Cr1 C7 C8 89.3(3)
C1 Cr1 C7 C8 168.3(3)
C3 Cr1 C7 C8 18.2(4)
C6 Cr1 C7 C8 -116.6(4)
C4 Cr1 C7 C8 -37.5(3)
C5 Cr1 C7 C8 -79.6(3)
I1 Cr1 C7 C8 -110.1(3)
C5 C4 C8 C7 0.5(5)
C9 C4 C8 C7 176.1(4)
Cr1 C4 C8 C7 -62.7(3)
C5 C4 C8 Cr1 63.2(3)
C9 C4 C8 Cr1 -121.2(4)
C6 C7 C8 C4 0.3(5)
Cr1 C7 C8 C4 63.7(3)
C6 C7 C8 Cr1 -63.4(3)
C2 Cr1 C8 C4 154.4(3)
C1 Cr1 C8 C4 -134.7(3)
C3 Cr1 C8 C4 75.3(3)
C7 Cr1 C8 C4 -117.3(4)
C6 Cr1 C8 C4 -79.7(3)
C5 Cr1 C8 C4 -37.9(2)
I1 Cr1 C8 C4 -2.0(4)
C2 Cr1 C8 C7 -88.3(3)
C1 Cr1 C8 C7 -17.4(5)
C3 Cr1 C8 C7 -167.4(3)
C6 Cr1 C8 C7 37.5(3)
C4 Cr1 C8 C7 117.3(4)
C5 Cr1 C8 C7 79.4(3)
I1 Cr1 C8 C7 115.3(3)
C8 C4 C9 C10 -92.1(5)
C5 C4 C9 C10 82.6(5)
Cr1 C4 C9 C10 177.9(3)
C4 C9 C10 N1 161.1(4)
C11 N1 C10 C9 51.2(5)
C13 N1 C10 C9 -71.2(5)
C12 N1 C10 C9 169.8(4)
